US7910678B2 - Copolymers having 1-methyl-2-methoxyethyl moieties - Google Patents

Copolymers having 1-methyl-2-methoxyethyl moieties Download PDF

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US7910678B2
US7910678B2 US11/942,700 US94270007A US7910678B2 US 7910678 B2 US7910678 B2 US 7910678B2 US 94270007 A US94270007 A US 94270007A US 7910678 B2 US7910678 B2 US 7910678B2
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Stephen Pacetti
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices

Definitions

  • Embodiments of the invention relate to polymeric coatings for coating implantable medical devices. More particularly, embodiments of the invention relate to copolymers that include a 1-methyl-2-methoxyethyl moiety and medical devices coated with the copolymers.
  • Implantable medical devices can be coated with polymers to give the implantable device beneficial properties when used in living tissue.
  • Implant coatings typically need to simultaneously fulfill many criteria.
  • desirable properties for implant coating properties include: adhesion to the implant (e.g., adhesion to stent struts) to prevent delamination; adequate elongation to accommodate implant deformation without buckling or cracking; sufficient hardness to withstand crimping operations without excessive damage; sterilizability; ability to control the release rate of a drug; biocompatibility including hemocompatibility and chronic vascular tissue compatibility; in the case of durable or permanent coatings, the polymer needs to be sufficiently biostable to avoid biocompatibility concerns; processability (e.g. production of stent coatings that are microns thick); reproducible and feasible polymer synthesis; and an adequately defined regulatory path.
  • methacrylate polymers exhibit several of the forgoing properties. However, most, if not all, methacrylate homopolymers lack a desired property or a combination of desired properties. For example, homopolymers of methyl methacrylate and ethyl methacrylate are too brittle. Homopolymers of n-butyl methacrylate (PBMA) are typically too hydrophobic for adequate drug elution (water absorption is only 0.4%).
  • PBMA n-butyl methacrylate
  • the polymer coatings of the invention include a hydrophobic monomer and a 1-methyl-2-methoxyethyl acrylate monomer (“MMOEA”) or a 1-methyl-2-methoxyethyl methacrylate monomer.
  • MOEA 1-methyl-2-methoxyethyl acrylate monomer
  • copolymers of the invention are biocompatible and suitable for use as coatings on implantable medical devices.
  • a copolymer according to the invention has the following formula.
  • m is in a range from about 0.1 to about 0.995
  • n is in a range from 0.005 to 0.9
  • R 1 is a straight chain, branched, unsaturated, or cyclic hydrocarbon having one to sixteen carbon atoms
  • R 2 and R 3 are independently a methyl or a hydrogen.
  • the combination of the MMOEA monomer with a hydrophobic monomer gives the copolymers of the invention good mechanical properties and useful drug permeability.
  • the polymer coating can be thermoplastic without cross-linking, which is beneficial for the elongation properties of the coating.
  • FIG. 1A illustrates an example of a stent coated with a co-polymer according to one embodiment of the invention
  • FIG. 1B is a cross-section of a strut of the stent of FIG. 1A .
  • Embodiments of the invention relate to copolymers suitable for use on implantable medical devices.
  • the copolymers include a hydrophobic monomer and an acryloyl or methacryloyl ester of a propylene glycol monomethyl ether, also referred to as 1-methyl-2-methoxyethyl acrylate (“MMOEA”).
  • MOEA 1-methyl-2-methoxyethyl acrylate
  • acrylate monomer includes, but is not limited to, methacrylates and acrylates.
  • the combination of the hydrophobic monomer and the MMOEA monomer advantageously provides desired mechanical strength, biocompatibility, and drug permeability in the copolymers of the invention.
  • the hydrophobic monomer is an acrylate monomer that includes hydrophobic groups attached through an ester linkage.
  • the hydrophobic group can be a straight chained, branched, unsaturated, or cyclic hydrocarbon.
  • the hydrophobic group is typically selected to give the copolymer a suitable water absorption, glass transition temperature, and mechanical strength without cross-linking.
  • hydrophobic monomers include, but are not limited to, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, isobutyl methacrylate, sec-butyl methacrylate, 2-ethyl-hexyl methacrylate, n-hexyl methacrylate, cyclohexyl methacrylate, n-hexyl methacrylate, isobornyl methacrylate, trimethylcyclohexyl methacrylate, combinations of these, and the like.
  • the MMEOA monomer is selected to increase water adsorption without adversely affecting the T g of the polymer coating.
  • the MMEOA monomer increases the water adsorption of the polymer coating because of the moderately polar groups in the side chain.
  • the MMEOA monomer can be an acrylate or a methacrylate.
  • the chemical structure of 1-methyl-2-methoxyethyl methacrylate (“MMEOM”) is shown below.
  • the alkoxy structure of the 1-methoxy-2-ethoxyethyl side group confers a degree of hydrophilicity that can be used to vary the water swelling property of the polymer. Varying the water swelling varies the drug permeability of the polymer coating.
  • the MMEOA monomer is copolymerized with a hydrophobic monomer.
  • the copolymer has the following formula.
  • the ratio of MMEOA monomer “n” to hydrophobic monomer “m” is selected to yield a copolymer with sufficient mechanical strength for use as a coating on an implantable medical device.
  • the concentration of MMEOA monomer is in a range from 10% to 99% and the concentration of hydrophobic monomer is in a range from 1% to 90%.
  • the copolymer can be tuned by adjusting the specific monomer ratio to achieve a desired mechanical strength and elongation.
  • the monomers shown in the chemical formula above and other chemical formulas herein can be in any order within the copolymer molecule and the monomer linkages shown in the chemical formulas only represent that the monomers are part of the same copolymer molecule.
  • the polymeric molecules can include monomers other than those shown in the chemical formulas.
  • the hydrophobic monomer is selected to yield a thermoplastic copolymer that is substantially free of cross-linking. While cross-linking can prevent excessive water swelling, cross-linking can be disadvantageous because it limits elongation, which leads to cracking of the polymer coating. Another benefit of a thermoplastic system is that it is simple to process compared to thermoset polymers.
  • the copolymers of the invention can also be made mechanically robust by increasing the copolymer's molecular weight.
  • the molecular weight of the copolymer can be increased as much as possible so long as processability is not compromised.
  • a high molecular weight yields a higher ultimate elongation for the polymer, which improves coating integrity.
  • high molecular weight typically yields better mechanical properties.
  • MMOEA monomer of the invention Another advantage of the MMOEA monomer of the invention is its biocompatibility. As shown in the chemical structure, the side group of MMOEA has the smallest PEG-type group possible, a single methoxyethyl group. PEG is known for its non-fouling or protein repelling properties.
  • the PMEA coating is the most hemocompatible of the polymers tested.
  • Kocakular et al. investigated the blood compatibility of PMEA coated extracorporeal circuits (Kocakular M., et al., J Bioactive and Compatible Polymers Vol. 17, September 2002, p. 343). Hollow fiber oxygenators coated with PMEA were evaluated during twenty clinical procedures requiring cardiopulmonary bypass. The operations were compared to twenty operations with uncoated hollow fiber oxygenators. PMEA coatings were found to reduce both platelet adhesion and fibrinogen/albumin absorption.
  • a coating of PEMA known as the X coating®, is used in the CAPIOX RX blood oxygenator sold by Terumo.
  • MMOEA Another benefit of MMOEA is the benign nature of its hydrolysis product.
  • the ester bond in MMOEA can potentially hydrolyze in vivo to form 1-methoxy-2-propanol, which is a solvent commonly known as “Dowanol PM”.
  • Dowanol PM The structure of 1-methoxy-2-propanol is shown below.
  • MMOE 1-methyl-2-methoxyethyl moiety
  • 1-methoxy-2-propanol is also very similar to 2-ethoxyethanol and 2-methoxyethanol in structure. Although these compounds are known to be teratogens, the toxicity of 1-methoxy-2-propanol is surprisingly in a range more similar to ethanol. A summary of the toxicity of these solvents is shown in Table 1.
  • the MMEOA monomer advantageously includes an alkoxy group, which is moderately hydrophilic, and useful for tuning the drug permeability, and mechanical robustness of the copolymer.
  • the toxicity of 1-methoxy-2-propanol is in a range that is similar to ethanol. Consequently, the MMEOA monomers of the invention can have the desired hydrophilicity and biocompatibility and are particularly suited for polymeric coatings used on permanent implantable devices.
  • the method of manufacturing the copolymers of the invention generally includes selecting or forming an MMEOA monomer and reacting the MMEOA monomer with a hydrophobic monomer to form a copolymer that is suitable for coating implantable medical devices.
  • the ratio of the hydrophobic monomer to the polar monomer By varying the ratio of the hydrophobic monomer to the polar monomer, the properties of the copolymer may be tuned.
  • the reaction mixture includes about 10% to about 99.5% of a hydrophobic monomer and about 0.5% to about 90% of a MMEOA monomer, based on the total moles of monomer in the reaction mixture.
  • the type and ratio of monomers is selected to yield a copolymer that is biocompatible and mechanically robust.
  • the copolymers can be synthesized using free radical polymerization, cationic polymerization, anionic polymerization, atom transfer radical polymerization, iniferter polymerization, or another suitable reaction technique.
  • Free radical polymerization can be carried out in a solvent using an initiator.
  • solvents suitable for carrying out the polymerization reaction include alcoholic solvents, such as, but not limited to, methanol, ethanol, and isopropyl alcohol.
  • suitable initiators for carrying out the polymerization reaction include peroxides, such as, but not limited to, benzoyl peroxide, and azo compounds.
  • a specific example of a suitable initiator is 2,2′-azo-bis(2-methylpropionitrile).
  • An alternate path to synthesizing the polymer includes copolymerizing a functional acrylate monomer and one or more hydrophobic monomers to yield a copolymer and then modifying the copolymer to include the MMOE group.
  • a functional methacrylate monomer and a hydrophobic monomer are reacted to yield the following copolymer.
  • the polymerization of this polymer can be carried out using the polymerization techniques described above. Thereafter, 1-methoxy-2-propanol is coupled to the carboxy groups of the methacrylic acid.
  • Several coupling chemistries are possible including conversion to the acid chloride or use of carbodiimides.
  • a particularly facile technique uses dicyclohexyl carbodiimide (DCC) and 4-(dimethylamino)pyridinium (DPTS) as described in M. Trollsas, J. Hedrick, Macromolecules 1998, 31, 4390-4395.
  • Yet another technique for synthesizing the MMEOA including copolymers begins with the homopolymer of the hydrophobic monomer.
  • the R 1 groups of this homopolymer can be exchanged off by catalytic esterification using an organic acid catalyst such as, but not limited to, p-toluene sulfonic acid in the presence of excess 1-methoxy-2-propanol.
  • an organic acid catalyst such as, but not limited to, p-toluene sulfonic acid in the presence of excess 1-methoxy-2-propanol.
  • the R 1 —OH alcohol so formed to be more volatile than the 1-methoxy-2-propanol (BP 119° C.) to facilitate its removal by distillation to drive the reaction.
  • methacrylates which are esters of methanol, ethanol, n-propanol, and isopropanol are more facile to process by this scheme than, for example, poly(n-butyl methacrylate) as the n-butanol boiling point (117° C.) is very close to that of 1-methoxy-2-propanol.
  • the copolymer compositions are manufactured to have a desired T g , when hydrated.
  • the T g of the copolymer can be calculated by knowing the amount of water absorbed and the T g derived from measurements of the homopolymer of the respective monomers. In an embodiment, the T g is calculated using the Fox equation, which is shown below.
  • T g Polymer W PC T g PC + W Water T g Water + W Methacrylate T g Methacrylate
  • the copolymer T g can be estimated with the desired target.
  • the desired target T g is in a range from about ⁇ 30° C. to about 37° C. when in the fully hydrated state.
  • the T g is between about 0° C. and about 37° C. when hydrated.
  • the copolymers of the invention will have a high degree of polymer mobility when placed in vivo. This feature allows the surface of the polymer to enrich in more hydrophilic MMEOA monomer content, which is advantageous for biocompatibility.
  • the co-polymer is designed to have a desired T g for the polymer in the dry state.
  • the T g of the polymer when dry is in a range from about ⁇ 30° C. to about 100° C. or in a range from about 0° C. to about 70° C.
  • the polymerization reaction can be controlled to produce the copolymers with a desired molecular weight.
  • the number average molecular weight of the copolymer is in the range from about 20K to about 800K, in another embodiment, the molecular weight is in a range from about 100K to about 600K.
  • the molecular weight of the polymer is selected to provide adhesion.
  • the molecular weight can be in a range from about 2K to about 200K.
  • the adhesive polymer can be used on medical devices that benefit from an adhesive polymer coating.
  • the copolymers of the invention are manufactured substantially free of cross-linking.
  • Copolymers manufactured according to the invention can have sufficient mechanical strength when hydrated that crosslinking is not necessary for making a polymer coating suitable for coating an implantable device.
  • the absence of cross-linking in the copolymers of the invention can give the copolymers improved elasticity, particularly when dry, which reduces the likelihood of cracking during assembly and use.
  • the MMEOA monomer can be made by reacting a polymerizable group with an 1-methoxy-2-propanol compound. These reactions are typically carried out using known reaction conditions. An example of a suitable reaction for forming a 1-methoxy-2-propanol substituted monomer is shown below.
  • 1-methoxy-2-propanol is reacted with methacryloyl chloride to yield 1-methyl-2-methoxyethyl methacrylate.
  • 1-methoxy-2-propanol and methacryloyl chloride are commercially available compounds (e.g., 1-methoxy-2-propanol is available from the Dow Chemical Company under the product name of “Dowanol PM”).
  • copolymers are suitable for use on any medical device that is compatible with polymer coatings.
  • the copolymers can be used alone as a coating or can be combined with other polymers or agents to form a polymer coating.
  • the polymers may be blended with poly(vinyl pyrrolidinone), poly(n-butyl methacrylate), poly(n-butyl methacrylate) copolymers, methacrylate polymers, acrylate polymers, and/or a terpolymers of hexyl methacrylate, vinyl acetate, and vinyl pyrrolidinone.
  • the polymer coatings can be applied to a medical device using any techniques known to those skilled in the art or those that may be developed for applying a coating to a medical device. Examples of suitable techniques for applying the coating to the medical device include spraying, dip coating, roll coating, spin coating, inkjet printing, powder coating, and direct application by brush or needle. One skilled in the art will appreciate the many different techniques in powder coating.
  • the copolymers can be applied directly to the surface of the implant device, or they can be applied over a primer or other coating material.
  • the polymer coatings are applied to a medical device using a solvent-based technique.
  • the polymer can be dissolved in the solvent to form a solution, which can be more easily applied to the medical device using one or more of the above mentioned techniques or another technique. Thereafter substantially all or a portion of the solvent can be removed to yield the polymer coating on a surface of the medical device.
  • suitable solvents include, but are not limited to, dimethylacetamide (DMAC), dimethylformamide (DMF), tetrahydrofuran (THF), dimethylsulfoxide (DMSO), cyclohexanone, xylene, toluene, acetone, i-propanol, methyl ethyl ketone, propylene glycol monomethyl ether, methyl t-butyl ketone, methyl isobutyl ketone, ethyl acetate, n-butyl acetate, n-butanol, ethanol, methanol, chloroform, trichloroethylene, 1,1,1-trichloreoethane, methylene chloride, cyclohexane, octane, n-hexane, pentane, and dioxane.
  • DMAC dimethylacetamide
  • DMF dimethylformamide
  • THF tetrahydrofuran
  • Solvent mixtures can be used as well.
  • Representative examples of the mixtures include, but are not limited to, DMAC and methanol (50:50 w/w); i-propanol and DMAC (80:20, 50:50, or 20:80 w/w); acetone and cyclohexanone (80:20, 50:50, or 20:80 w/w); acetone and xylene (50:50 w/w); acetone, xylene and F LUX R EMOVER AMS® (93.7% 3,3-dichloro-1,1,1,2,2-pentafluoropropane and 1,3-dichloro-1,1,2,2,3-pentafluoropropane, and the balance is methanol with trace amounts of nitromethane; Tech Spray, Inc.) (10:40:50 w/w); and 1,1,2-trichloroethane and chloroform (80:20 w/w).
  • suitable implantable devices that can be coated with the copolymers of the invention include coronary stents, peripheral stents, catheters, arterio-venous grafts, by-pass grafts, pacemaker and defibrillator leads, anastomotic clips, arterial closure devices, patent foramen ovale closure devices, and drug delivery balloons.
  • the copolymers are particularly suitable for permanently implanted medical devices.
  • the implantable device can be made of any suitable biocompatible materials, including biostable and bioabsorbable materials.
  • suitable biocompatible metallic materials include, but are not limited to, stainless steel, tantalum, titanium alloys (including nitinol), and cobalt alloys (including cobalt-chromium-nickel and cobalt-chromium-tungsten alloys).
  • Suitable nonmetallic biocompatible materials include, but are not limited to, polyamides, fluoropolymers, polyolefins (i.e. polypropylene, polyethylene etc.), nonabsorbable polyesters (i.e. polyethylene terephthalate), and bioabsorbable aliphatic polyesters (i.e. homopolymers and copolymers of lactic acid, glycolic acid, lactide, glycolide, para-dioxanone, trimethylene carbonate, ⁇ -caprolactone, and the like, and combinations of these).
  • the copolymers are particularly advantageous as a coating for stents due to their elongation properties, which allows the coated stent to be crimped and expanded without cracking the coating.
  • the stents can be composed of wire structures, flat perforated structures that are subsequently rolled to form tubular structures, or cylindrical structures that are woven, wrapped, drilled, etched or cut.
  • FIG. 1A shows an example stent 10 coated with a copolymer including MMEOA monomers.
  • Stent 10 includes a generally tubular body 12 with a lumen.
  • the struts of body 12 e.g. strut 14
  • FIG. 1B illustrates a cross-section of the stent of FIG. 1A coated with a polymer coating 16 .
  • the polymer coating 16 can be conformal as in FIG. 1B .
  • the coating can be ablumenal, luminal, or any combination thereof.
  • the copolymers of the invention are elastic at body temperatures and can therefore expand without cracking as the stent expands during use.
  • the polymer coated stents of the invention can be self-expanding or balloon expandable.
  • the copolymer coatings of the invention can be particularly advantageous for self-expanding stents.
  • Self-expanding stents are typically restrained by a sheath that is removed during deployment of the stent.
  • the copolymers of the invention can have improved mechanical strength to better withstand the friction exerted on the polymer as the sheath is removed.
  • a bioactive agent is associated with the coated medical devices of the invention.
  • the bioactive agent can be associated with a base coat, top coat, mixed with the novel copolymers of the invention, and/or incorporated or otherwise applied to a supporting structure of the medical device.
  • the bioactive agent can have any therapeutic effect.
  • suitable therapeutic properties include anti-proliferative, anti-inflammatory, antineoplastic, antiplatelet, anti-coagulant, anti-fibrin, antithrombonic, antimitotic, antibiotic, antiallergic and antioxidant properties.
  • bioactive agents include synthetic inorganic and organic compounds, proteins and peptides, polysaccharides and other sugars, lipids, DNA and RNA nucleic acid sequences, antisense oligonucleotides, antibodies, receptor ligands, enzymes, adhesion peptides, blood clot agents, including streptokinase and tissue plasminogen activator, antigens, hormones, growth factors, ribozymes, retroviral vectors, anti-proliferative agents including rapamycin (sirolimus), 40-O-(2-hydroxyethyl)rapamycin (everolimus), 40-O-(3-hydroxypropyl)rapamycin, 40-O-(2-hydroxyethyoxy)ethylrapamycin, 40-O-tetrazolylrapamycin (zotarolimus, ABT-578), 40-epi-(N-1-tetrazolyl)-rapamycin, 40-O-[2-(2-hydroxy)
  • a coated stent can be used in, but is not limited to use in, neurological, carotid, coronary, aorta, renal, biliary, ureter, iliac, femoral, and popliteal vessels.
  • copolymers of MMEOM monomers and hydrophobic monomers are specific examples of copolymers of MMEOM monomers and hydrophobic monomers.
  • the following copolymers are useful for coating implantable medical devices.
  • Example 1 describes a copolymer of poly(1-methyl-2-methoxyethyl methacrylate-co-n-butyl methacrylate) (poly(MMOEM-co-n-butyl methacrylate)).
  • the poly(MMOEM-co-n-butyl methacrylate) polymer has the following formula.
  • m is in a range from 0.25 to 0.995 and n is in a range from 0.005 to 0.75.
  • poly(n-butyl methacrylate) monomer is particularly advantageous since the homopolymer of PBMA is currently being used in implantable medical devices and is thus known to be biocompatible.
  • Example 2 describes a copolymer of poly(1-methyl-2-methoxyethyl methacrylate-co-ethyl methacrylate) (poly(MMOEM-co-ethyl methacrylate)).
  • poly(MMOEM-co-ethyl methacrylate) The chemical formula of poly(MMOEM-co-ethyl methacrylate) is shown below.
  • m is in a range from 0.25 to 0.99 and n is in a range from 0.01 to 0.75.
  • T g of the alkyl methacrylate monomer enables a harder, stronger coating at the expense of elasticity as compared to the copolymer of Example 1.
  • Example 3 describes a method for manufacturing a coated stent using the polymers of Examples 1 and/or 2.
  • a primer coating is applied to the stent.
  • a primer solution including between about 0.1 mass % and about 15 mass %, (e.g., about 2.0 mass %) of poly(n-butyl methacrylate) (PBMA) and the balance, a solvent mixture of acetone and cyclohexanone (having about 70 mass % of acetone and about 30 mass % of cyclohexanone) is prepared.
  • PBMA poly(n-butyl methacrylate)
  • the solution is applied onto a stent to form a primer layer.
  • a spray apparatus e.g., Sono-Tek MicroMist spray nozzle, manufactured by Sono-Tek Corporation of Milton, N.Y.
  • the spray apparatus is an ultrasonic atomizer with a gas entrainment stream.
  • a syringe pump is used to supply the coating solution to the nozzle.
  • the composition is atomized by ultrasonic energy and applied to the stent surfaces.
  • a useful nozzle to stent distance is about 20 mm to about 40 mm at an ultrasonic power of about one watt to about two watts.
  • the stent is optionally rotated about its longitudinal axis, at a speed of 100 to about 600 rpm, for example, about 400 rpm.
  • the stent is also linearly moved along the same axis during the application.
  • the primer solution is applied to a 15 mm Triplex, N stent (available from Abbott Vascular Corporation) in a series of 20-second passes, to deposit, for example, 20 ⁇ g of coating per spray pass. Between the spray passes, the stent is allowed to dry for about 10 seconds to about 30 seconds at ambient temperature. Four spray passes can be applied, followed by baking the primer layer at about 80° C. for about 1 hour. As a result, a primer layer can be formed having a solids content of about 80 ⁇ g.
  • Solids means the amount of the dry residue deposited on the stent after all volatile organic compounds (e.g., the solvent) have been removed.
  • a copolymer solution is prepared.
  • the copolymer solution includes the copolymer of Examples 1 and/or Example 2.
  • the solution is prepared by dissolving between about 0.1 mass % and about 15 mass %, (e.g., about 2.0 mass %) of the copolymer in a solvent.
  • the solvent can be a mixture of about 70 mass % acetone and about 30 mass % cyclohexanone.
  • the copolymer solution is applied to a stent. Twenty spray passes are performed with a coating application of 10 ug per pass, with a drying time between passes of 10 seconds, followed by baking the copolymer layer at about 60° C. for about 1 hour, to form a layer having a solids content between about 30 ⁇ g and 750 ⁇ g, (e.g., about 200 ⁇ g).
  • Example 4 describes a method for manufacturing a drug eluting stent according to the invention.
  • the medical device is manufactured using the same method as in Example 3, except that instead of the copolymer solution, a polymer-therapeutic solution is prepared and applied using the following formula.
  • a drug-including formulation is prepared that includes:
  • the drug-including formulation is applied to the stent in a manner similar to the application of the copolymer solution in Example 3.
  • the process results in the formation of a drug-polymer reservoir layer having a solids content between about 30 ⁇ g and 750 ⁇ g, (e.g., about 200 ⁇ g), and a drug content of between about 10 ⁇ g and about 250 ⁇ g, (e.g., about 67 ⁇ g).
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